The Winter Meetings are slated to begin on Monday and the Chicago Cubs could be making headlines when it’s all said and done.
The Chicago Cubs will enter 2025 with a 5-year playoff drought that they will be hoping to end. If they have any hopes of trying to end that drought, they will need to be very active during this year’s Winter Meetings. They enter the Winter Meetings primed to do so, with the 4th ranked farm system in all the MLB per Bleacher Report, the Chicago Cubs could practically make as many moves as they would like for the type guys on any team’s roster. The only question still yet to be answered is, will the Cubs spend some money to do so? That really depends on if they can trade a player like Cody Bellinger.
Cody Bellinger is the Chicago Cubs biggest question mark coming into the Winter Meetings. Since picking up his $27.5M option for this year the Cubs have been looking for any chance to get rid of his salary so they can then allocate those freed up funds to put toward a top arm for the rotation. Sadly, any move for Bellinger will have to wait until Juan Soto decides to sign with a team.
Being that one of teams in on Bellinger are the New York Yankees, who are also in on Soto, until the find out what he’s doing Bellinger’s market will remain stagnate. That decision by Soto could come by the middle to the end of the Winter Meetings however, so Bellinger’s market could quickly “heat up” as Bruce Levine of 670 The Score put it.
Another odd thing to note is that it was reported by the New York Post Joel Sherman that the Chicago Cubs are “determined” to move off of outfielder/DH Seiya Suzuki’s contract as well if they can’t get off of Bellinger’s that is. Suzuki is still under club control for another two seasons where he’s owed $19M both in 2025 and 2026 according to Baseball Reference.
Moving off of a player like Suzuki in my opinion would not be smart. Yes, could he bring back value like a number two or possibly an “Ace” like starter yes, but why would the Cubs do that and deplete their offense? It also would be tricky to do so being he has a full no-trade clause in his contract.
So far in three seasons with the Cubs Suzuki has a career slash line of .278/.354/.470 with an OPS and OPS+ of .824 and 128. Even though Suzuki isn’t the best defender in right field he does provide the Cubs with adequate defense while playing out there sporting a career .983 fielding percentage. With Suzuki set to take more reps at the DH spot this year trading away his bat would not be advisable for the Cubs in my opinion.
What do the Chicago Cubs Need?
The Chicago Cubs at the Winter Meetings have three holes that they need to fill for next season. They are: 1. Finding an “Ace” level starter for the rotation 2. Securing a backend of the bullpen arm either for the 7th or 8th innings or a Closer and 3. Getting a catcher to either pair with Miguel Amaya or upgrading the position. All three of these needs could all potentially be filled by the end of the Winter Meetings with pitching being of abundance this year.
Starting Pitching
Starting pitching is the top priority for the Cubs entering the Winter Meetings. Whether that’s them adding it through a trade like getting Logan Gilbert, or them moving off Bellinger’s contract so they can go out and spend on a top arm like Corbin Burnes. However, pitchers like Walker Buehler, who according to MLB Trade Rumors have the Cubs “considering” him, as well as The Athletic Sahadev Sharma and Patrick Mooney reporting it as well. Buehler could be a very valuable option for the Cubs if they signed him.
Coming off a season where he was working his way back from Tommy John surgery in which he went 1-6 with a 5.38 ERA in 75.1 innings Buehler could provide a cheap, but high upside type of signing. The Cubs just signed LHP Matt Boyd to a two-year $29M deal with $1M in incentives bringing it to $30M ($15M per) total. Buehler is a far better pitcher than Boyd, and so I would say possibly giving Buehler a four-year/$70M ($17.5M) with an opt-out after the second year I believe would get the job done.
Another arm that the Chicago Cubs should look to target at the Winter Meetings is one of Walker Beuhlers teammates from last year and that’s fellow World Series Champion Jack Flaherty. Flaherty who will enter his age 29 season come 2025 had a solid year overall. Pitching for both the Detroit Tigers and Los Angeles Dodgers Flaherty went 13-7 with a 3.17 ERA in 28 starts, 194 strikeouts, a WHIP of 1.068 in 162 innings. For the post season however, Flaherty didn’t impress. In two starts (10 innings) in the NLCS Flaherty had a 7.20 ERA and in two starts (6.2 innings) in the World Series he had an 8.10 ERA.
Flaherty would be getting a different deal than I had for Walker Buehler being that he was relatively healthy and pitched a full season. If you look at the recent starting pitchers who were signed so far like LHP Yusei Kikuchi signing a three-year $63M ($21M) deal with the Los Angeles Angels, LHP Blake Snell signing a five-year $182M ($36.4M) deal with the Los Angeles Dodgers, or RHP Nick Martinez accepting the qualifying offer ($21.05M) with the Cincinatti Reds Flaherty fits somewhere in there.
Entering the Winter Meetings Flaherty is going to be looking for a long-term deal. He certainly won’t get anywhere near the amount of money that Blake Snell received, but I do think that he will get the same number of years. I think if the Cubs want to sign someone like Jack Flaherty at the Winter Meetings they’ll need to give him somewhere around $23M AAV (average annual value) to get it done. He in my opinion is on par if not slightly better than someone like Yusei Kikuchi who is making $21M next year. So, if he’s looking for a five-year deal, then I think something like five-year for $115M ($23M) would be acceptable for someone like Flaherty.
Michael Lorenzen would be an interesting target for the Chicago Cubs to look to sign at the Winter Meetings. A respectable pitcher with a career ERA of 3.99 Lorenzen would be a solid option for the rotation. Coming off a season where he pitched for both the Texas Ranger and Kansas City Royals where in total, Lorenzen had a 7-6 record with a 3.31 ERA with 97 strikeouts, and 60 walks in 24 starts (130.1 total innings pitched).
Lorenzen, who will be 33 come the start of the season, is going into the Winter Meetings primed to be paid. With the Cubs in need of right-handed starting pitchers Lorenzen would slot in well with a rotation set to already have the likes of Shota Imanaga, Justin Steele, Jameson Taillon, the newly added Matthew Boyd, as well as Javier Assad and Jordan Wicks as depth pieces. He could easily slot into the number two or three spots in the rotation depending on how Craig Counsel wanted to break up Imanaga and Steele.
The Chicago Cubs appear to be big fans of giving out short term deals to pitchers in their early 30’s just take Jameson Taillon, Shota Imanaga, and the new signed Matthew Boyd be the examples. So why not dish out another at this year’s Winter Meetings to Michael Lorenzen. Being Lorenzen is the same age as Jameson Taillon, both are relatively similar as starting pitchers with the slight edge being given to Taillon, given the fact that Lorenzen was used as a reliever throughout his career which affects his career innings totals 854.1 compared to Taillon’s 1107.1. Both sport almost similar ERAs Lorenzen has a career 3.99 while Taillon has a 3.89 ERA.
The Chicago Cubs signed Jameson Taillon to a four-year $68M deal back at this time at the 2022 Winter Meetings. So, at this year’s Winter Meetings with the Cubs primed to do the same thing Micheal Lorenzen would appear to be the next Jameson Taillon signing. Being Lorenzen is two years older than Taillon was when he signed his deal (31), I think a three-year deal anywhere between $48-$51M plus a team option for a fourth year to bring the total deal to somewhere between $64-$68M gets things done.
Trades
I have a strong feeling the Cubs will be lighting the trade market a blaze once the Winter Meetings get underway. Once Juan Soto signs Cody Bellinger will be one of the hotter commodities even given his price tag of $27.5M. Teams like the New York Yankees, Houston Astros, and the Seattle Mariners have all check in on players like Cody Bellinger and second basemen Nico Hoerner. All three teams need offense (in particular the Mariners), and all three teams need either a first basemen or outfield help.
I believe if the New York Yankees can’t resign Juan Soto than Cody Bellinger will be their next target. With the ability to take on the money with close to $70.5M coming off their books and with them needing someone to play either first base or center field with the Yankees being able to move Aaron Judge back over to right field where he’s more suited to play.
With the Cubs needing catching and with not many to choose from on the free agency market at the Winter Meeting I believe they should look to target the New York Yankees number 30th ranked prospect Rafel Flores as their top guy in the return. Flores at both High-A and Double-A combined (122 games) hit .279/.379/.495 for an OPS of .874 along with 31 doubles and 21 HRs. So, if I were the Chicago Cubs I would offer the Yankees a deal like this:
The New York Yankees receive: first basemen/outfielder Cody Bellinger
The Chicago Cubs receive: starting pitcher Marcus Stroman and catcher/first basemen Rafel Flores
The Yankees are heavily targeting Juan Soto and hope to get a deal done with him during the Winter Meetings, but if they could swing a trade for Bellinger that wouldn’t be a bad consolation prize to take back from the Winter Meetings. Bellinger would provide a solid bat to put either behind or in front of Judge as well as someone capable of playing Gold Glove defense at both first base and center field.
For the Chicago Cubs they would be leaving the Winter Meetings fulfilling the needs of securing a right-handed starter for the rotation in Marcus Stroman who they are familiar with, as well as more catching depth and a potential flier in Flores who could turn into a solid or even possibly an everyday player once called up.
Out of the Box Trade for the Winter Meetings
A trade that I think that could possibly happen is a trade between the Toronto Blue Jays and Chicago Cubs. The Blue Jays could use someone to pair with Vladimir Guerrero Jr. at first base as well as at the DH spot. I think Cody Bellinger would be a perfect partner to pair with Vladdy since there’s no real drop off defensively between the two and Bellinger’s bat has the potential to bounce back.
Alejandro Kirk who is only 26 years old would be a great if not solid pickup for the Cubs to get at the Winter Meetings in a surprise deal. Kirk according to Baseball Savant Kirk ranks in the 95th percentile for caught stealing above average with 7 and the 93rd percentile for framing. Kirk also boosts a 33% caught stealing percentage which lead to him throwing out 20 would be base stealers. Kirk would also provide a solid bat even though he’s had a couple of down seasons. For his career Kirk has a slash line of .264/.344/.391 with and OPS and OPS+ of .735 107.
The Toronto Blue Jays receive: first basemen/outfielder Cody Bellinger and second basemen Nico Hoerner
The Chicago Cubs receive: Catcher Alejandro Kirk, RHP José Berríos, and RHP Landen Maroudis (Blue Jays #14 prospect)
This would be a great deal for both teams in my eyes to walk out of the Winter Meetings with pulling off. As I said the Blue Jays get a bat and partner to pair with Vladdy at first base and DH spot as well as an upgrade at second base with the acquisition of Nico Hoerner. As of now looking at the Blue Jays depth chart right now Spencer Horwitz and Davis Schneider will platoon there. This also of course hinges in if the Blue Jays land Juan Soto at the Winter Meetings being they are one of the final teams in contention for him.
The Bullpen
The last thing needing addressed at the Winter Meetings is the bullpen. The Chicago Cubs need a lockdown Closer or at the very least a high-end backend of the bullpen arm. The top option for me isn’t someone like a Tanner Scott or a Jeff Hoffman, but I believe the Cubs should target LHP Danny Coulombe who last pitched for the Baltimore Orioles last two seasons. Last year with Baltimore Coulombe had a 1-0 record with a 2.12 ERA and 32 strikeouts in 29.2 innings. The ten-year veteran lefty just turned 35 back in October and still has a lot left in the tank given he’s had a below 3 ERA the past three seasons.
The Orioles decided to decline Coulombe’s team option which would’ve cost them $4M an increase of $1.7M from his $2.3M salary for 2024. I believe that is slightly high for someone like Coulombe given his age. Aroldis Chapman just received a one-year $10.75M deal with the Boston Red Sox which Coulombe will get nowhere near. However fellow bullpen arms T.J. McFarland (35) signed with the Athletics for one-year worth $1.8M deal as well as Justin Wilson (37) got a one-year $2.25M deal from the Red Sox.
I believe if the Chicago Cubs decided to give Danny Coulombe a two-year deal worth $6M ($3M per year) I think that would be just about right to sign him. The Cubs need another lefty for the bullpen being they have none at the moment unless Jordan Wicks gets moved there to pair with him. Coulombe also has experience pitching late in games which is also a plus for the Cubs.
Another under the radar signing the Chicago Cubs could make at the Winter Meetings for a Closer could be for someone like Paul Sewald. Sewald would provide the Cubs someone with experience not only at the backend of games but also has closing experience. This year teams at the Winter Meetings are very limited with their options for pitchers who have closing experience. The best options available are Devin Williams and Ryan Helsley, but teams have to trade for them. The top Closer on the market is LHP Tanner Scott who won’t be cheap, and the Cubs appear to be out on, so Paul Sewald would be an excellent backup option.
Sewald in his career has a total of 84 saves in 376.1 career innings. Someone who won’t light up the radar gun like a Chapman, but he has stuff and is able to get the job done and has proven he can handle the pressure. A one-year prove it deal worth around $8M is what I think would get the job done.
The last bullpen piece the Cubs should look to target at the Winter Meetings is former Cub Andrew Chafin who pitched for the team from 2020-2021. Last season between the Detroit Tigers and Texas Rangers Chafin pitched in 62 games (56.1 innings) where he had a 3.51 ERA with 70 strikeouts. Chafin would provide solid middle relief help in the Cubs bullpen capable of pitching someone in the 5th-7th innings. I’d say a deal similar to like Coulombe’s is in order for Chafin however just a one-year deal worth $4M is what I think would be a good fit for Chafin.
The Winter Meetings are primed to be a very exciting time for baseball. The possibility that Juan Soto signs during the Winter Meetings is very high and we will potentially a flurry of trades from all teams, but I think the Cubs will be at the center of a decent amount.
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